Questions tagged [inductive-effect]
Use for questions regarding the so called inductive effect of substituents on properties of compounds.
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Comparing stability of acetate and formate with respect to inductive effect
According to my teacher, the order for +I effect is
$$\ce{-CH2-} > \ce{-NH^-} > \ce{-O^-} > \ce{-COO^-} > \ce{-R} > \ce{-H}.$$
So, $\ce{-COO^-}$ must have more pronounced +I effect ...
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Acidity of toluene compared to propyne
Why is propyne more acidic than toluene? The carbanion formed in case of toluene is easily stabilised by resonance and -I effect of toluene. In case of propyne there is an electron donating ...
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what role does mesomeric effect and inductive effect play in stability of carbocations in presence of halogens
what should be the ideal explanation behind the order of stability of these three compounds?
Case-1
In these three examples the first two structures have a positive mesomeric effect and it is greater ...
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Stability of phenylic carbocations [closed]
Problem:
Structure (1) is more stable than structure (2).
My teacher stated that Structure (1) is more stable than Structure (2). I find this confusing. How can Structure (1) be more stable when ...
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If a compound has a strong and weak minus I group, will the stronger group always have a δ- charge?
In a compound like acrolein (prop-2-enal or $\ce{CH2=CH-CHO}$, will the oxygen in the $\ce{-CHO}$ group always have a $\delta$- charge?
Acrolein does have three resonance structures as shown below, ...
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Inductive Effect (R-NH3+ and R-NH2)
Textbooks I've read state that R-NH3+ has exhibits a greater -I inductive effect than R-NH2 does.
However, I've also read in places that the + charge in R-NH3+ only represents a formal charge and has ...
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Can alkyl groups show -I effect?
Inductive effect is the partial shifting of the sigma-bonding electrons towards more EN (take as electronegativity or electronegative in this text) atom so why we will say that alkyl groups will ...
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Is there a quantitative definition of inductive effect?
Usually, Inductive effects are compared using the electronegativities and distances. However, this only works in compounds with similar structures. For example, we can predict the following orders of ...
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+M or -I for chlorine? Major product in free radical chlorination and bromination of 2-chloropropane?
Is the +M or -I effect more dominant in when an alkyl (mono)halide is subject to free radical chlorination/bromination?
For example what will be the major product in case of free radical (mono)...
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Why is the melting point of 4-bromoacetanilide so high? Does it have any reason to do with the chemical structure, or the para aspect?
We used melting point to determine the type of bromoacetanilide, and it was closest to 4-bromoacetanilide. How can I explain why the melting point was what it is?
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Acidic strength of nitrophenols
I've seen the pKa values of Nitrophenol as follows:-
pKa of o-nitrophenol= 7.23
pKa of p-nitrohenol= 7.14
so p-nitrophenol is more acidic than p-nitrophenol
But both phenoxide ions are stabilized ...
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Acidic strength order among hydroxytetralones [closed]
I can understand in 1 the conjugate base has more stability for better resonance but in 2 and 3 the effect of resonance cannot be considered. How can we compare the inductive effect in such case?
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Why is the inductive effect possible?
Firstly, I must preface that I am a Biology student. To elaborate my question, I was looking for the reason why carboxylic acids are more acidic than alcohols, despite both compounds containing —OH ...
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Is NH2 electron donating or electron withdrawing? [closed]
Can anyone explain why NH2 shows -I in inductive effect and +R in resonance effect? I mean NH2 is ready to take electrons in inductive effect (with its electronegativity) but in the resonance effect, ...
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Is Bent's Rule an alternative explanation for the Inductive Effect?
Today I read that Bent's Rule can be used to explain the inductive effect (I was reading the Consequences section of this Wikipedia article). If I understand it correctly, for a molecule CL3R, the ...
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Effect of beta branching and carbocation rearrangement on SN1 reaction rates
My book (NCERT class 12 Chemistry) asks
Predict the order of reactivity of the four isomeric bromobutanes in SN1 and SN2 reactions.
The answer given for SN1 is
1-bromobutane < 1-bromo-2-...
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How to establish trend of carboxylic acid acidity in the presence of certain substituents?
I encountered a question in my textbook which asked the following:
At first, i thought that i can approach it in the same way i sort the effect of EDG and EWG on the acidity of phenols, that is, ...
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What is the correct order of Relative Inductive Effect (-I) of different groups?
This confusion has put me in problem several times since last 2 years and I have been looking for a clarification but it seems that answer depends upon who you ask. I have several examples where I ...
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Effect of electron-donating and electron-withdrawing groups on the C=O bond
My notes states this:
An electronegative element tends to draw in the electrons between the carbon and oxygen atoms through its electron-withdrawing effect. This strengthens the C=O bond.
An electron-...
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Comparing acidic strength of acetic and p-anisic acids
In p-anisic acid the phenyl ring with methoxy group acts as strong electron donating group by mesomeric effect (+M), whereas in acetic acid there is only an electron donating nature by inductive ...
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Reactivity of Alkenes with HBr [closed]
I am new in the Organic Chemistry (World of Reactions). I had got one question in my test. But, when I had seen it, I got no proper logic to tick the correct answer, and then when I saw solution, then ...
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Inductive Effect of -CH3 group [duplicate]
3° carbocations are the most stable because of the +I effect of -CH3 group. This group gives a slight negative charge to the central carbon atom, which makes it less positively charged and thus, more ...
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Does inductive effect operate through pi bonds?
I have been told that the inductive effect is only present in sigma bonds by my teacher, and the book I've referenced also says the same thing.
However, I can't think of why this is. Answers to this ...
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Why does chlorine show a mesomeric effect in haloarenes and an inductive effect in haloalkanes?
Chlorine shows the +R effect in haloarenes and the -I effect in haloalkanes. Does chlorine do the same for all cyclic compounds or only for aromatic rings? Is this just another experimentally seen ...
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Difference between nucleophilicity of phenoxide ion and acetate anion in protic/aprotic solvent
As far as I could think, the phenoxide ion is comparatively larger as compared to acetate ion, so it should undergo less solvation in presence of a protic solvent and thus its nucleophilicty should be ...
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Ortho effect and the relative acidity in aromatic acids [duplicate]
What is the order of the acidity of 2-methyl benzoic acid and 2-isopropyl benzoic acid?
I know about ortho effect which states that the acidity of ortho- substituted aromatic carboxylic acids is ...
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How come the methyl group (-CH3) is electron donating?
If the inductive effect operates purely through electronegativity differences, how come the methyl group is considered to donate electrons through the inductive effect? My textbook says that there is ...
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Why is the carbanion stability order the way it is? (3*<2*<1*)
According to the lecture notes I made, a 1* carbanion is more stable than a 3* carbanion. I can't grasp exactly why. (I had a look at the similar questions, the answers didn't help)
With my very ...
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Hydrogen as a reference in inductive effect
What does it mean when we say that I-effect of hydrogen is taken as zero ?
I think that it means that partial displacement of sigma bond electrons between two atoms of different electronegativity is ...
user108965
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Why don't we consider the attached hydrogens in inductive effect?
Consider the molecule 1-chloroethane
Let carbon attached to $\ce{Cl}$ be $\ce{C1}$ and other one be $\ce{C2}$. While learning inductive effect I was told that $\ce{Cl}$ due to high electronegativity ...
user108965
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Why is ethanol more acidic than acetone?
The acidity of a compound is determined by the stability of its conjugate base and the major structure of enolate has a negative charge on the Oxygen atom. Moreover, the negative charge on the O-atom ...
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Effect of distance on the mesomeric effect
I have always thought that mesomeric effect is somewhat dependent on distance.
But I recently came across a question where I was asked to predict the order of stability of o-methoxyphenyl carbocation ...
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Why hydrogen bonding in some acids make them a stronger acid when it is present even before deprotonation?
If we take the example of salicylic acid, hydrogen bonding is present in the acid as follows:
Even after deprotonation, it has intramolecular hydrogen bonding as follows:
My question:
p-...
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Stability of meta ethyl and meta methyl benzene carbocations respectively
It is known that Methyl has a greater +I effect than Ethyl, but here, in this case, the condition is satisfied in the para benzene carbocations whereas, in the meta forms, it is the opposite. Shouldn'...
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Carbocation formation and stability from bromo compounds
When heated,the following bromo-species all form carbocations via $\sigma$ bond cleavage. For each structure draw the corresponding carbocation and briefly describe how it is stabilised.
This is my ...
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Comparing nucleophilic strengths of tetrahydropyran and (2R,6R)-2,6 dimethyltetrahydropyran
Compare the nucleophilic strengths of the following two compounds:
According to me it should be the second one, that is, (2R,6R)-2,6-dimethyltetrahydropyran because the methyl groups would exert +I ...
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How do steric effects affect inductive effect in compounds with tetravalent nitrogen?
I want to compare the electron density on methyl group between tri‐tert‐butyl(methyl)azanium (1) and triisopropyl(methyl)azanium (2), i.e. essentially the inductive effects of $\ce{-\overset{+}{N}R3}$ ...
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Evaluating inductive effects in cyclic compounds
I was required to find the products on heating the hydroxide of;
Now it's easy enough to find the answer; Hoffman elimination isn't going to happen from the methyl, and the n-propyl doesn't have $\...
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Acidic nature comparison; benzoic acid and phenylacetic acid
The $\ce{pK_a}$ values of benzoic acid and phenylacetic acid are around 4.2 and 4.31 respectively.
In benzoic acid, you have the resonance being the dominating effect, destabilizing a conjugate base ...
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What does acidity of para-alkyl substituted phenols depend on?
Problem
Arrange the following organic compounds in decreasing order of acidity.
Answer
Question
According to my knowledge the answer should be P, Q, R, S. As we proceed from P to S we are ...
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Stabilization of multiple bonds through inductive effects
In the conversion of m-chloroanisole to m-anisidine using $\ce{NaNH2}$ and liquid $\ce{NH3}$, apparently the reason the $\ce{NH2-}$ goes for the meta- position instead of the para position is that, in ...
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Why does the carboxylate ion show positive inductive effect?
While solving some problems on general organic chemistry, I came across this question that asked for the nature of inductive effects of $\ce{-CH_3}, \ce{-CO_2^-}, \ce{-Br}, \ce{-NH_3^+}$.
And in the ...
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Confusion in comparing the contribution of resonating structures to resonance hybrid [closed]
So I was comparing the $+M$ effect of $\ce{-CH^-_2}$, $\ce{-NH^-}$ and $\ce{-O^-}$. Answer was given as:
$$ \ce{-CH^-2 > -NH^- > -O^-}$$
So, I attach them with ethene and made their respective ...
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Relative acidity of acetic acid derivatives with strongly withdrawing substituents
What would be the order of $\mathrm{p}K_\mathrm{a}$ values of the following:
$\ce{O2N-CH2-CO2H},$
$\ce{Me3\overset{+}{N}-CH2-CO2H},$
$\ce{NC-CH2-CO2H},$
$\ce{HO-CH2-CO2H}?$
Since only the groups ...
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Combined Effect of Steric Inhibition of Resonance and Inductive Effect
While qualitatively comparing the acidic nature of o-methyl benzoic acid and benzoic acid, we consider the steric effect due to which the $\ce{-COOH}$ group loses its planarity and the +M effect of $\...
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How to explain regioselectivity in nucleophilic aromatic substitution
I’m trying to rationalise the major regioisomeric product of the following reaction of an arylchloride in the presence of sodium amide:
I have predicted that the para-substituted product is formed as ...
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Order of −I effect among ethenyl and 1-propenyl groups
We know that both ethenyl $\ce{-CH=CH}_2$ and 1-propenyl $\ce{-CH=CH-CH3}$ are electron-withdrawing groups when attached to hydrocarbon chain. Which one has greater electron withdrawing power?
The $\...
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Does the benzene ring in styrene show a negative inductive effect on the ethenyl group?
I know that a group exerts an inductive effect on another one if there is a difference in electronegativity. In the case of styrene (1) all the atoms are sp2-hybridized. So, how could the phenyl ring ...
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Estimation of dipole moments in aromatic compounds
If it asks to compare dipole moment in aromatic compounds then do we see inductive or resonance effects or do we see a mix of both?
E.g. we have to compare dipole moment in pyrrole and furan then in ...
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Comparing reactivity of 1-chloroethane and 1-chloropropane in an SN1 reaction
Beginning with a reference to a well known question.
Order by reactivity towards SN1 reaction.
According to some facts about SN1 reactions, rate depends on:
Stability of carbocations
Better leaving ...
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